Abiotic Fe(III) induced mineralization of phenolic substances

Pracht, Jens; Boenigk, J; Isenbeck‐Schröter, Margot; Keppler, Frank; Schöler, H. F.

doi:10.1016/s0045-6535(00)00490-2

Cited by 85 publications

(68 citation statements)

References 14 publications

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“…It is also known that while quinones are reduced may cause oxidation of other molecules involved in the redox cycle like other 1,2-DHB (107,108) . The quinones can also be oxidized to CO 2 while reducing Fe 3+ (109) (110,111) .…”

Section: Dhb Driven Fenton Reactionmentioning

confidence: 99%

Fenton Reaction Driven by Iron Ligands

Salgado

Melín

Contreras

et al. 2013

J. Chil. Chem. Soc.

107

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One of the most important sources of reactive oxygen species (ROS) in biological systems is the Fenton reaction. In this, the Fe 2+ or Fe 3+ reacts with H 2 O 2 to produce ROS as the hydroxyl radical (•OH), superoxide radical (O 2 •-) and singlet oxygen ( 1 O 2 ). The main ROS, responsible for the high oxidizing power of the Fenton reaction, is not clear. Some authors claim that the principal reactive species is •OH, while others propose a ferryl specie (Fe 4+ or [FeO] 2+ ) (1,2) . Recently, have been proposed that the kind of reaction species produced depends mainly of pH and the iron composition of the coordination sphere. This is highlighted for Fe 3+ , because in mono and (some) bis-complexes Fe 3+ is reduced to Fe 2+ and there are some positions occupied by water or hydroxide ligands, readily to be exchanged by H 2 O 2 . On the other hand, in tris-complexes there are not any positions occupied by water or hydroxide, avoiding the formation of peroxo-complexes, necessary for Fenton or Fenton like reaction.The 1,2-dihydroxybenzenes (DHBs) have been described as modulators of Fenton reaction. The DHBs driven Fenton reaction have been used for environmental applications as an advanced oxidation process. Furthermore, these systems participate in different biological process, as the wood biodegradation by fungi and oxidative stress in neurodegenerative diseases.In this review, the effect of 1,2-dihydroxybenzenes on the activated species production by the Fenton and Fenton like reaction will be discussed and its participation in different systems.

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Section: Dhb Driven Fenton Reactionmentioning

confidence: 99%

Fenton Reaction Driven by Iron Ligands

Salgado

Melín

Contreras

et al. 2013

J. Chil. Chem. Soc.

107

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“…Recently, Pracht et al (2001) investigated the abiotic mineralization of phenolic model substances with Fe 3þ . The liberation of CO 2 points to a cleavage of the aromatic ring.…”

Section: Model Substances Considered As Natural Organic Matter Form Hmentioning

confidence: 99%

Formation of chloroacetic acids from soil, humic acid and phenolic moieties

2003

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The mechanism of formation of chloroacetates, which are important toxic environmental substances, has been controversial. Whereas the anthropogenic production has been well established, a natural formation has also been suggested. In this study the natural formation of chloroacetic acids from soil, as well as from humic material which is present in soil and from phenolic model substances has been investigated. It is shown that chloroacetates are formed from humic material with a linear relationship between the amount of humic acid used and chloroacetates found. More dichloroacetate (DCA) than trichloroacetate (TCA) is produced. The addition of Fe 2þ , Fe 3þ and H 2 O 2 leads to an increased yield. NaCl was added as a source of chloride. We further examined the relationship between the structure and reactivity of phenolic substances, which can be considered as monomeric units of humic acids. Ethoxyphenol with built-in ethyl groups forms large amounts of DCA and TCA. The experiments with phenoxyacetic acid yielded large amounts of monochloroacetate (MCA). With other phenolic substances a ring cleavage was observed. Our investigations indicate that chloroacetates are formed abiotically from humic material and soils in addition to their known biotic mode of formation.

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“…A closer look at the oxidative capabilities of Fe III demonstrated the mineralisation of catechol to CO 2 , [159] and the formation of chloroethene and chloroalkanes from catechol under Fenton-like conditions in the presence of chloride. [160] The degradation of catechol to mono-and dicarboxylic acids was observed, [162,163,164] and chloroethyne, [165] carbon suboxide [166] and trihalomethanes [167] were also detected.…”

Section: Modelling Of the Catalytically Active Iron Speciesmentioning

confidence: 99%

“…The latter is assumed to be an intermediate in the mineralisation process [159] and the formation of saturated and unsaturated halocarbons, [160,165] see Fig. 11 and Abiotic oxidation of organic matter section.…”

Section: Modelling Of the Catalytically Active Iron Speciesmentioning

confidence: 99%

“…Based on studies with several phenolic derivatives (catechol, hydroquinone, and recorcinol), [166,167] [159] (2) chloroethene and chloroalkanes, [160] (3) chlorinated acetic acid, [118,161] (4) muconic, formic, acetic, oxalic, malonic, fumaric and maleic acids, [162][163][164] (5) chloroethyne, [165] (6) carbon suboxide, [166] (7) trihalomethanes, [167] (8) furan. [168,169] In the corresponding enzymes and model systems, the iron species are transformed to the resting state, top left.…”

Section: Modelling Of the Catalytically Active Iron Speciesmentioning

confidence: 99%

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Iron-catalysed oxidation and halogenation of organic matter in nature

et al. 2015

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Environmental context. Natural organohalogens produced in and released from soils are of utmost importance for ozone depletion in the stratosphere. Formation mechanisms of natural organohalogens are reviewed with particular attention to recent advances in biomimetic chemistry as well as in radical-based Fenton chemistry. Iron-catalysed oxidation in biotic and abiotic systems converts organic matter in nature to organohalogens.Abstract. Natural and anthropogenic organic matter is continuously transformed by abiotic and biotic processes in the biosphere. These reactions include partial and complete oxidation (mineralisation) or reduction of organic matter, depending on the redox milieu. Products of these transformations are, among others, volatile substances with atmospheric relevance, e.g. CO 2 , alkanes and organohalogens. Natural organohalogens, produced in and released from soils and salt surfaces, are of utmost importance for stratospheric (e.g. CH 3 Cl, CH 3 Br for ozone depletion) and tropospheric (e.g. Br 2 , BrCl, Cl 2 , HOCl, HOBr, ClNO 2 , BrNO 2 and BrONO 2 for the bromine explosion in polar, marine and continental boundary layers, and I 2 , CH 3 I, CH 2 I 2 for reactive iodine chemistry, leading to new particle formation) chemistry, and pose a hazard to terrestrial ecosystems (e.g. halogenated carbonic acids such as trichloroacetic acid). Mechanisms for the formation of volatile hydrocarbons and oxygenated as well as halogenated derivatives are reviewed with particular attention paid to recent advances in the field of mechanistic studies of relevant enzymes and biomimetic chemistry as well as radical-based processes.

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Abiotic Fe(III) induced mineralization of phenolic substances

Cited by 85 publications

References 14 publications

Fenton Reaction Driven by Iron Ligands

Fenton Reaction Driven by Iron Ligands

Formation of chloroacetic acids from soil, humic acid and phenolic moieties

Iron-catalysed oxidation and halogenation of organic matter in nature

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